Dimethylformamide dimethyl acetal → HCID 54017096, compound

HRID 1290823Notes

Reaction equation

HRID 1290823 reaction equation
[C:1]([O:9][CH:10]([CH3:14])[C:11](=[O:13])[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[C:1]([O:9][CH:10]([CH3:14])[C:11](=[O:13])[CH:12]=[CH:17][N:18]([CH3:20])[CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2319833-oxobutan-2-yl benzoate

Product 1

HCID 54017096HCID 54017096, compound

Procedure

A mixture of 3-benzoyloxybutan-2-one (15.5 g) and dimethylformamide dimethylacetal (14.4 g) was heated on a steam bath for 2 hours 30 minutes. The solvent was removed from the mixture under reduced pressure. Petroleum ether (b.p. 60°-80° C.) was added to the residue, with shaking and the ether layer separated from an insoluble red oil. Further petroleum ether was added to the oil with shaking and excess ether was removed under reduced pressure to give a red-brown oil which partially crystallised on standing overnight. Petroleum ether was added and the solid was collected by filtration and washed with petroleum ether to give a yellow crystalline solid of 4-benzoyloxy-1-dimethylamino-1-penten-3-one. Yield 5.6 g. The solid was used directly without further purification in the next step.

Workup

  1. temperaturewas heated on a steam bath for 2 hours 30 minutes
  2. customThe solvent was removed from the mixture under reduced pressure
  3. additionPetroleum ether (b.p. 60°-80° C.) was added to the residue
  4. customthe ether layer separated from an insoluble red oil
  5. additionFurther petroleum ether was added to the oil
  6. stirringwith shaking
  7. customexcess ether was removed under reduced pressure
  8. customto give a red-brown oil which
  9. custompartially crystallised
  10. additionPetroleum ether was added
  11. filtrationthe solid was collected by filtration
  12. washwashed with petroleum ether

Sources & evidence

ORD record
ord-d5e221e9437649fca574fea1b2a00e2c
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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